Methyl morpholine oxide → benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate

HRID 906947ノート

反応式

HRID 906947 の反応式
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH3:17].C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:17][C@H:3]1[C:2](=[O:1])[CH2:6][CH2:5][N:4]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

参加物

5

反応物 2

HCID 82029Methyl morpholine oxideHCID 59556882benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

生成物 1

HCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate収率 89%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

To a solution (150 mL) of benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate (20.5 g) in acetonitrile were added molecular sieves 4A powder (25 g) and 4-methylmorpholine-N-oxide (20.4 g), and the mixture was cooled to 0° C. tetra-n-Propylammonium perruthenate (3.0 g) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate. The insoluble material was filtered through Hyflo Super-Cel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→2/1) to give the title compound as a colorless oil (yield: 18.0 g, yield: 89%).

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationThe insoluble material was filtered through Hyflo Super-Cel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→2/1)

出典と根拠

ORDレコード
ord-cd3e8c0fa6454dd3b82ac968c58a9e17
出典データセット
uspto-grants-2011_09
特許番号
US08013008B2

反応ノート

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